Good Times and Sad Tales in Jack Kerouac’s St. Pete

Day-drinking, riding bikes, and remembering a literary icon; Last Sunday was a perfect afternoon for all of those things as a hundred or so people came together to learn more about the somewhat dismal final chapter of the life of author and poet, Jack Kerouac.

Known and beloved for his role as one of the Beat Generation’s defining writers, Kerouac spent much of the last few years of his life in St. Petersburg in the late 1960s. Places he lived, drank, frequented and died, were all part of the tour called “Kerouac in Paradise: A Literary Bike Tour of St. Petersburg”, created by St. Pete native, Margaret Murray, as part of her graduate thesis.

Under a cloudless blue sky, folks of all ages in flip-flops, tennis shoes, khaki shorts, and skinny-jeans, riding rusty beach-cruisers and well-maintained road bikes, converged on The Flamingo Bar where Kerouac is known to have imbibed on the reg. A few of us sipped Bloody Marys, others just listened quietly as Murray played a recording of a friend of Kerouac’s telling a story about him. The gist was that Kerouac was somewhat of a wildcard, provocative and improvisational. We learned over the course of the ride that these qualities, combined with his heavy use of booze, left him a sad and sick man at the end of his life.

The first stop on the tour was the St. Petersburg Police Department, where he ended up when he was arrested in 1964 for public urination, though that wasn’t the only time he’d spent the night there. Murray told the crowd about how Kerouac had always been close with his small immediate family- his mother and sister, but in the later years of his life, things between them had become strained. That’s how things still stood when his sister died suddenly of a heart attack. Upon learning of his estranged sister’s death he was deeply upset that things ended like that, and went on a pretty solid bender around town. The drunken-spree ended with the public urination arrest, but Kerouac’s regret over the rift was said to have stayed with him until his death five years later.

Next we rode to Haslam’s book store, where Kerouac was known to rearrange his own books so that they’d be more prominently displayed. Murray said he also did things like tuck certain other authors, like Ken Kesey’s, books out of view. Some even say Kerouac’s ghost still haunts Haslam’s. Murray told us that according to an owner, sometimes when they’re alone in the book store a book will fall off the shelf, and it’s usually a Kerouac book. Hmmmm.

During the years Kerouac was in St. Pete, on and off from 1964 to 1969, there were 137 bars in town, 13 movie theaters, and four book stores, according to Murray’s research. These were the types of places he liked to go in the town he sometimes called the “home of the newlywed and living dead,” or “nearly dead,” depending on which report you read.

￼Though he was a serious drinker, (by today’s standards he’d pretty much be considered a raging alcoholic) he never lost his ability to write a great story, as we learned at the next stop outside of the Tampa Bay Times (Formerly St. Pete Times, formerly The Evening Independent) building where Murray told us Kerouac showed up drunk with a friend and some beers to share. A former athlete and avid sports fan, he told the reporter who was there at the time he wanted to write articles for the sports section. The story goes that he convinced the reporter to sit back and drink a beer while Kerouac typed up the article the reporter was struggling with. Kerouac finished the article in about an hour, along with two others. No edits were necessary.

Next we rode across the busy thoroughfares of 34th and 49th Streets North, with the help of our trusty bike-guides holding off traffic, heading toward the house Kerouac owned with his third wife, Stella, whom he married in 1966. The home has been vacant since her death in 1990, but the group “Friends of the Jack Kerouac House” are working to maintain it and have it declared a historical landmark. The $10 registration fee for the bike tour was used toward this purpose. The President and Vice President of the FOTJKH were there and spoke to the crowd about their hopes for the house where Kerouac spent his last, lonely days.

At the simple brick and white-washed wooden house in the Disston Heights neighborhood, people often still leave notes in the mailbox. There was one that day. It said, “Jack, You make the sky less empty. Love, Steve.”

In an article in The Tampa Bay Times, a reporter who visited him at the house in 1969 described how he found Kerouac sitting in front of a muted television, listening to Handel on his record player, smoking a cigarette, drinking whiskey from a pill bottle and chasing it with a beer. He told the reporter he was lonely. He felt like crap. He had a hernia. Kerouac seemed all together miserable. Murray said that he self-treated the hernia by scotch-taping a 50-cent piece over it. Murray also told us that by then, Kerouac had alienated most of his friends and family. He was often in physical fights because he was obnoxious and obstinate. He racked up big long-distance bills drunk- dialing anyone who would listen to him anymore. He had cirrhosis of the liver.

Weeks after this visit from the reporter, on Oct 21, he died of a hemorrhage at St. Anthony’s Hospital, the last stop on the tour. According to a recorded interview with a friend who was there, Kerouac started vomiting blood at home, then went to the hospital where he fought and flailed, only to die after hours of useless blood transfusions.

On that dark note, and after a thirst-inducing bike ride, we went back to The Flamingo and toasted Kerouac with his signature drink combination, a shot of whisky chased with beer, a.k.a, a “shot and a wash”. It seemed a fitting way to end the tour, and probably the way Kerouac would’ve done it.

Though his last years in St. Petersburg were not his best years, always beneath Kerouac’s drunken debauchery and storied ravings was his love and mastery of the written word. Besides his classic American novels, like “On The Road, and “The Dharma Bums”, Kerouac was a poet. His carefully crafted simple Haikus are a reminder that though his life came to a bitter end, he seemed to appreciate much of life’s little beautiful moments, and this bike tour and the camaraderie it created counted for one of life’s beautiful times for me. I leave you with a few of Kerouac’s Haikus.